(2S)-2-(2-azaniumylacetamido)-3-phenylpropanoate

Base Information

• Chemical Name: (2S)-2-(2-azaniumylacetamido)-3-phenylpropanoate
• CAS No.: 3321-03-7
• Molecular Formula: C11H14 N2 O3
• Molecular Weight: 222.244
• Hs Code.: 2924299090
• Mol file: 3321-03-7.mol

Synonyms:Gly-L-Phe;GF zwitterion;Gly-Phe zwitterion;Gly-L-Phe zwitterion;glycylphenylalanine zwitterion;BDBM36082;glycyl-L-phenylalanine zwitterion;CHEBI:133047;(2S)-2-(2-azaniumylacetamido)-3-phenylpropanoate

Chemical Property of (2S)-2-(2-azaniumylacetamido)-3-phenylpropanoate

Chemical Property:

• Appearance/Colour: Crystalline
• Vapor Pressure: 1.67E-10mmHg at 25°C
• Melting Point: ~264 °C (dec.)
• Refractive Index: 41 ° (C=2, H2O)
• Boiling Point: 492.2°Cat760mmHg
• Flash Point: 251.5°C
• PSA: 92.42000
• Density: 1.259g/cm³
• LogP: 0.84840
• Storage Temp.: −20°C
• Water Solubility.: almost transparency
• XLogP3: -1.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 222.10044231
• Heavy Atom Count: 16
• Complexity: 244

Purity/Quality:

98%,99%, ^*data from raw suppliers

Gly-Phe-OH ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CC(C(=O)[O-])NC(=O)C[NH3+]
• Isomeric SMILES: C1=CC=C(C=C1)C[C@@H](C(=O)[O-])NC(=O)C[NH3+]
• Uses: Glycyl-DL-phenylalanine is used in methods and composition for spacial and temporal measurement of catalytic activity.

Technology Process of (2S)-2-(2-azaniumylacetamido)-3-phenylpropanoate

There total 21 articles about (2S)-2-(2-azaniumylacetamido)-3-phenylpropanoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

metronidazole glycyl phenylalaninate hydrochloride (145615-35-6) → Gly-Phe-OH (3321-03-7) + metronidazole (443-48-1) + cyclo(Gly-Phe) (5037-75-2,10125-07-2,23927-19-7)

Guidance literature:

With aqueous buffer; Rate constant; pHs 0.83-8.82, half-life times for the hydrolysis, also in simulated intestinal fluid (pH 7.55), Jones medium (pH 6.69) and Kupferberg medium (pH 6.11);

Reference yield:

Z-Gly-(L)-Phe (1170-76-9) → Gly-Phe-OH (3321-03-7)

Guidance literature:

With methanol; palladium; acetic acid; Hydrogenation;

Reference yield:

L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) → Gly-Phe-OH (3321-03-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / Et₃N / tetrahydrofuran; H₂O / 20 °C

2: H₂ / Pd/C / methanol / 3 h / 25 °C / 1551.49 Torr

With hydrogen; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; water; 1: Condensation / 2: Hydrogenolysis;

DOI:10.1021/jm990226g

upstream raw materials:

N-phthaloylglycine chloride

L-phenylalanine

Z-Gly-(L)-Phe

Z-Gly-L-Phe-OBzl

Downstream raw materials:

Trt-Gly-Phe-Gly-Gly-OH

Trt-Gly-Phe-Gly-Gly-OBn

C₆₁H₆₁N₅O₁₅

L-phenylalanine

Refernces

• 1、 Ohara-Nemoto, Yuko,Rouf, Shakh M. A.,Naito, Mariko,Yanase, Amie,Tetsuo, Fumi,Ono, Toshio,Kobayakawa, Takeshi,Shimoyama, Yu,Kimura, Shigenobu,Nakayama, Koji,Saiki, Keitarou,Konishi, Kiyoshi,Nemoto, Takayuki K.. "Identification and characterization of prokaryotic dipeptidyl-peptidase 5 from porphyromonas gingivalis". . p. 5436 - 5448. Retrieved 2014/03/21.
• 2、 Ganellin, C. Robin,Bishop, Paul B.,Bambal, Ramesh B.,Chan, Suzanne M. T.,Law, James K.,Marabout, Benoit,Luthra, Pratibha Mehta,Moore, Andrew N. J.,Peschard, Olivier,Bourgeat, Pierre,Rose, Christiane,Vargas, Froylan,Schwartz, Jean-Charles. "Inhibitors of tripeptidyl peptidase II. 2. Generation of the first novel lead inhibitor of cholecystokinin-8-inactivating peptidase: A strategy for the design of peptidase inhibitors". . p. 664 - 674. Retrieved 2007/10/03.